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Org Lett. 2013 Aug 2;15(15):3914-7. doi: 10.1021/ol4016749. Epub 2013 Jul 12.

One-pot asymmetric synthesis of seven-membered carbocycles cyclohepta[b]indoles via a sequential organocatalytic Michael/double Friedel-Crafts alkylation reaction.

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1
Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, 621, Taiwan, ROC.

Abstract

A new method has been developed for the enantioselective synthesis of highly functionalized cyclohepta[b]indoles with high enantioselectivity (up to 96% ee). The process combines an enantioselective organocatalytic Michael addition and a highly efficient double Friedel-Crafts reaction sequence in one pot with good yields and stereoselectivity. The structures and absolute configurations of the products were confirmed by X-ray analysis.

PMID:
23848568
DOI:
10.1021/ol4016749
[Indexed for MEDLINE]
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